Peter DeCaprio Insights

Credit · Public equities · Market structure

Where Venture Debt Fits in a Lower Middle Market Capital Stack

Where venture debt fits between the bank that says not yet and the equity round that costs too much, laid out layer by layer down the capital stack.

Peter DeCaprio seated on the edge of a desk at the front of a classroom, listening to a student's question with a blackboard behind him
Peter DeCaprio taking questions in a finance class. The capital stack is usually the first thing worth drawing on the board.

Start with the problem, because the instrument only makes sense once the problem is clear.

A company has something customers pay for. Revenue arrives every month and most of it comes back the next month. The founders have a plan that needs another year or two of spending before the business turns a profit, and they can show you where that spending goes. They take this to their bank. The bank reads the same numbers and sees losses, thin hard collateral, and a borrower whose value sits in code, contracts and people rather than in trucks and buildings. However warm the relationship, the answer is some version of not yet.

So the founders turn to their equity investors, who are willing, but at a price that resets the ownership of the company and on terms that follow every later round. The distance between what a bank will underwrite and what new equity costs is where venture debt lives. It is not a better bank loan and it is not cheaper equity. It is a different instrument with its own logic, easiest to see when the whole stack is laid out at once.

The stack, top to bottom

LayerWhat it costs the companyWhat it demandsWhen it fits
Senior secured bank debtThe cheapest money availableHard collateral, positive cash flow, tight covenants and a first claim on everythingA profitable business with assets a bank could actually sell
Venture debtMore than a bank, far less than equity, plus a small warrantA credible equity sponsor, a clear use of proceeds, a lien on the business and real information rightsA growing company that has proved demand but not yet proved profit
Subordinated and mezzanine debtA high coupon, often partly paid in kindPatience on repayment, a claim behind the senior lender and a slice of the upsideA business with steady cash flow that has used up its senior capacity
Preferred equityA share of ownership with a preference on the way outBoard rights, protective provisions and a liquidation preference ahead of commonA company raising real growth capital from investors who want downside protection
Common equityThe most expensive capital there is, because it is permanent and last in lineBelief in the plan, and control of whatever remains after everyone else is paidFounding, and the moments when the future is genuinely open

Read down the table and the pattern shows itself.

Each layer trades price for protection.

The senior lender is cheap because it can take the assets. Common equity is dear because it gets whatever is left. Venture debt sits in the middle. It is cheaper than any form of equity precisely because it is repaid first, and dearer than a bank because it lends against a plan rather than a warehouse. The warrant is the lender admitting that some of the risk it carries is equity risk, and asking to be paid for that part in equity.

Three situations where it earns its place

Bridging to a milestone

The cleanest use is a bridge. The company is a few quarters from an event that will change how it is valued: a product release, a contract that has been signed but not yet billed, a break-even month that the model shows clearly. Raising equity before that event means selling ownership at the old price. A loan sized to reach the milestone, with a little cushion, lets the company arrive at the next round on its own terms. If the milestone slips, the loan is still there and the runway is shorter.

Extending runway without a down round

The second use is defensive. Markets turn, and a company that was worth one figure to investors last year is worth less this year through no fault of its own. Raising now would reset the price for every holder, including employees. A modest facility can carry the business through the trough so that the next equity conversation happens in a better market. This is the use I am most careful with, because it works only when the business is fundamentally sound and the trough is a market event rather than a company event. Debt does not fix a broken model. It gives a broken model more time to prove it is broken.

Funding a specific asset

The third use is the most conventional. The company needs equipment, a fleet, a build-out, the purchase of a smaller competitor, something with a definable cost and a definable return. Nobody should give up permanent ownership to buy something that will pay for itself within a few years. A term loan matched to the life of the asset, secured by the asset where possible, is the right tool.

What I ask before I lend

  • Who is the equity sponsor, how much have they put in, and would they put in more if the plan slipped? A lender in this layer is underwriting the sponsor’s next decision.
  • Where exactly does the money go, month by month, and what does the business look like at the end of it?
  • What is the real gross margin on the revenue, after the costs the company prefers to show further down the page?
  • What is the downside case, and does the loan still get repaid in it? Not the model the company sends. The one I build.
  • If the plan stumbles, does the structure give an early signal, in the form of a covenant, a reporting requirement or a reserve, before the money is gone?
  • If the business were sold tomorrow at a disappointing price, where would this loan sit in the waterfall?
  • Do I understand the product well enough to explain, in one plain paragraph, why customers keep paying for it?

A tool, not a strategy

Venture debt is a tool with a narrow set of jobs, and it does those jobs well. It buys time, it protects ownership, and it finances things that ought to be financed rather than bought with equity. It does not make a weak company strong and it does not replace the discipline of raising the right amount of equity at the right moment. The companies that use it best treat it the way a good builder treats a power tool: chosen for one task, used with attention, and put down when the task is done. The ones that get hurt are the ones that reached for it because it was the easiest capital to get.

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